Org. Lett. [SOPHY]

Abstract

We report herein a domino reaction to construct 2-amido-5-fluoropyrroles from CF₃-substituted N-allenamides. The in situ generated gem-difluorinated ene-ynamides derived from CF₃-substituted N-allenamides, when subjected to silver catalysis with a primary amine, undergo simultaneous hydroamination of the ynamide moiety followed by a 5-endo-trig addition/β-fluoride elimination sequence, enabling the construction of 2-amido-5-fluoropyrroles. This transformation features excellent functional group compatibility. By employing 2-aminophenols, functionalized benzo-oxazoles were produced.

Reference

Silver-Catalyzed Domino Reaction of CF₃Substituted N-Allenamides with Primary Amines for the Construction of 2-Amido-5-fluoropyrroles

Maxime Hourtoule and Laurence Miesch

Org. Lett. , Publication date March 6 – DOI: https://doi.org/10.1021/acs.orglett.3c00401

 

Contact

Laurence Miesch (team SOPhy), Institut de Chimie de Strasbourg (UMR 7177).